Aliphatic C–H activation with aluminium trichloride–acetyl chloride: Expanding the scope of the Baddeley reaction for the functionalisation of saturated hydrocarbons

The functionalisation of decalin by means of an “aliphatic Friedel–Crafts” reaction was reported over fifty
years ago by Baddeley et al. This protocol is of current relevance in the context of C–H activation and
here we demonstrate its applicability to a range of other saturated hydrocarbons. Structural elucidation
of the products is described and a mechanistic rationale for their formation is presented. The “aliphatic
Friedel–Crafts” procedure allows for production of novel oxygenated building blocks from abundant
hydrocarbons and as such can be considered to add significant synthetic value in a single step.